I remember Kripke saying many years ago something like "it's not going to end well for the Winchesters." I have always regretted that we could never see his original vision for the show. The first few seasons were amazing.
I kind of liked the ending we got, but original it was not. It is a big-time rip off of Six Feet Under's ending.
I saw them both. Not sure how it's that close to Lost.
The Six Feet Under ending with Claire driving, and we see everyone live their lives right up to their deaths is an exact mirror of Dean driving and us seeing Sam live his life right up to his death. Complete with cool music on both.
I don't remember every chacaracter who survived but Hugo and Benjamin lived their full lives as island caretakers and died of old age, yet they all met up in purgatory and moved on to heaven together with the rest of them.